Masters of MEDDICC: Lucy Williams-Jones

00:00 Andy Whyte: Hello and welcome to episode number eight of Masters of MEDDICC. I'm here with Lucy Williams-Jones. Welcome, Lucy. How are you doing?. 00:05 Lucy Williams-Jones: I'm brilliant, thank you. 00:10 Andy Whyte: Yeah. And I'm very happy that you're here as well, because this has been a very long time coming. I think I've been trying to get you on this show for maybe a year now, maybe even longer. 00:25 Lucy Williams-Jones: I don't know if it's been that long. 00:25 Andy Whyte: It has been that long. 00:25 Lucy Williams-Jones: And the Covid lockdown — I think my answer was: I need to get to the hairdressers first. But I'm fine now. 00:25 Andy Whyte: Yeah. Happy days. You got there. I don't have that excuse in my locker for obvious reasons. But I'm very, very glad you're here. 00:43 Andy Whyte: And perhaps before we get started, I want to start with something that stood out for me — maybe the reason you and I got to know each other in the first place. Can you guess what it is? Why I first reached out to you, Lucy?. 01:05 Lucy Williams-Jones: I would say because of my background with various PTC-lineage companies and my adoption of MEDDIC over the past ten years. 01:05 Andy Whyte: Yes, that's kind of the start of it — but there was something in particular that really stood out. When I was researching the book, I was going down this rabbit hole of PTC alumni companies and great organisations, looking for people to do research with. And I stumbled — as you do in those LinkedIn rabbit holes of "people also viewed" — on your profile. And there was one thing that stood out: back-to-back Presidents Clubs for, I think at the time, something like 19 years. 01:50 Lucy Williams-Jones: Is that right?. 01:50 Andy Whyte: Exactly. You must have started your sales career at about age ten to fit that many in. But yeah — tell us a little about yourself and your career. I'm very excited to hear it. 02:09 Lucy Williams-Jones: Absolutely. So I fell into tech when I was 18 years old, and it's probably one of the best decisions I ever made. I make three great decisions in my career. The first one was not going to university. I was 18, I had a place at Manchester Met to do physiotherapy and sports therapy, and I decided to take a gap year to see the world and live a little before buckling down. And then one of my very good friends, Richard Maguire — he's since emigrated — said: "We've got this role at a software company where you can do part admin, part sales and see if you like it." I thought: the pay's great and I'll learn some new stuff. I said yeah. I stayed for 14 years. 02:46 Andy Whyte: A quick dash!. 02:46 Lucy Williams-Jones: So I joined on 25th October 2000 — 22 years ago next week as we're recording this. I joined Quest Software. And before inside sales was really prevalent, I was doing a bit of admin, getting the faxes when fax machines were a thing, processing orders. And I was also doing some outbound calling. Within about six months I moved into a proper inside sales role, which I was in for about two years. And through that my career progressed — I became an AE, an enterprise AE specialising in systems integration for local government, which was a booming market at the time. And then I moved to Ireland to manage the database unit for monitoring tools at Quest. Actually a cool place to be. So 14 years — a long time to stay at one company — but probably one of the best and most formative periods of my career. Not only did I make some amazing friends, but we all grew up in it together. And Quest, the going rate of £80 a day — it's a numbers game at that level. When we got our copy of the Yellow Pages, we were told: go sell Oracle database development tools. So that's what we did. And we had territories — A to C, D to F — and we'd all sit in this hothouse. 04:07 Lucy Williams-Jones: It was in Burnham, and we'd sit there, and Mary Acuna — who I think is now at ServiceNow — would be getting us fired up: "Come on, let's get more calls, more groups!" Numbers on the board, and you never wanted to be at the bottom. We made a great company even better. And that's when the income came, and it created a real family. Simon Pierce, who was the MD of the UK — we all grew up together. And now I look at all the people I worked with back then — they've all gone on to do great things. People who went to Splunk, people at various other companies. But we are still really tight. We built that little community. Some of them are my bridesmaids. We've been to each other's weddings. So I spent 14 years at Quest. And although I loved my time there, I wanted to come back to London. So I thought: do I get transferred back and continue selling for Quest — the company I'd been with for 14 years, selling database development tools — or do I take a new challenge? So I came back and did a short stint at Couchbase, in that leadership space. Great experience. 05:15 Lucy Williams-Jones: I spent about ten months there, and dipped my toe into MEDDIC. They wanted to be a MEDDIC company — but did they truly live the playbook? I'd maybe disagree on that. But I spent about ten months there and then realised databases were maybe a little bit boring, however good the technology was. I got headhunted by a great recruiter who put me into BMC — and I think that's where my career really changed. I did BMC for about two and a half years, selling monitoring again — back to what I'd been doing at Quest. So it was my safe space, working with large enterprise accounts like Vodafone, EDF Energy, and HSBC. I really loved it. I was very fortunate to learn so much from great leaders — I worked directly for some excellent managers, and I was working with Steve Hamilton in the majors team and under Don Darcy before he moved over to MongoDB. And I learned so many amazing things. As a PTC-lineage MEDDIC company, BMC are probably one of the best at driving the playbook and articulating why MEDDIC is so important within a sales cycle. 06:37 Lucy Williams-Jones: From that point I thought: I'm never going to work for a non-MEDDIC company again. 06:37 Andy Whyte: And have you ever found yourself in that position — being courted by a company for an opportunity, and the fact that they don't use MEDDIC becomes a genuine decision criterion?. 06:37 Lucy Williams-Jones: 100%. I use your website actually — I know that's used by many companies now. Yeah, absolutely. I believe in the playbook wholeheartedly. My team today talk about it all day long. And I think if you can follow that process as a team, you're going to be able to not only accelerate any sales cycle, but give a great customer experience. And that's what matters most, right? It's not all about closing a transaction — it's about making sure there's an exchange of value, and that both organisations benefit. That's what the playbook enables. 07:25 Andy Whyte: Yeah, I love that. And I think that's the thing — people often ask me what's the most common misconception about MEDDIC. There are a lot of them, and usually when you dig in you find the person hasn't really looked into it or properly used it. But the one I think is strongest is this idea that MEDDIC is somehow not a good experience for the customer — when for me it's the complete opposite. Think back to where it originated: it came from reverse-engineering why customers buy and don't buy. If that's your blueprint — building a framework around the positive and negative decisions customers make — you can only be right. So yeah, it's fascinating to hear you describe it that way. 08:07 Lucy Williams-Jones: And that's absolutely it. So after BMC, a chunk of that team moved over to MongoDB. I'd already touched NoSQL at Couchbase, so I thought: now's the time. And with everything, timing is so important. So I moved to MongoDB and again learned some amazing things from great people like the sales leaders there — very much that PTC way of working. And again, MongoDB running the playbook really well and doing extremely well as a result. When I left there — and although I was super excited about Datadog because monitoring had always been my safe space — I also had to leave behind some really fond memories of how we'd sit in war rooms, using those spaces when incidents went down in organisations, and thinking: how do we transact, and how do we build something that delivers real customer value — for the likes of RBS or HSBC? So I left MongoDB in December 2018 and joined Datadog on 11th January 2019. I always leap between years — I never take a summer off, it's always Christmas and New Year. So I started on the 11th, 2019. Coming up for four years now. I did two and a half years as an individual contributor, looking after a number of strategic accounts, and then more recently — six months ago — I got promoted to one of the Regional Directors there as well. 10:31 Lucy Williams-Jones: So again, the PTC legends theme continues — I'm now working across a team of five or six enterprise reps looking after enterprise accounts in UK and Ireland. 10:57 Andy Whyte: Well, first of all — and I've said this to you before but for the podcast — congratulations on the promotion. Very well deserved. And it's always a challenging thing to step up and manage a team you used to be part of. But I know you hit the ground running. How many new people have you had to hire?. 11:18 Lucy Williams-Jones: I've personally hired five new people. But across Datadog UK we're hiring aggressively to handle the growth. We've got three teams now, each going up to six people, and we're looking to expand again next year. The market is booming, especially in digital. 11:18 Andy Whyte: So yeah — how have you found the recruiting process? Starting to hire people and getting into that role?. 11:51 Lucy Williams-Jones: I actually really enjoy the recruiting side because it's kind of like a sales process. And I'm engineered as a salesperson deep down. I had a very specific wish list of what I was looking for, and I think I've achieved it. I'm super happy with my team — a real mixture. But one of the fundamental things they all have is some MEDDIC and Command of the Message background, whether they've used it extensively before or not. They're all aware of it. And other qualification methodologies — like the ones we used to have 20 years ago — they're just not as structured. Yeah. So I've found the recruitment really interesting. I'm really enjoying it. I've got five new hires right now who are at 30, 60, or 90 days, and I'm trying to ramp them as quickly as possible so I can start delivering value to customers — which is super, super important to me. 12:55 Andy Whyte: Yeah, I love that. I was reading an article you did recently that talked about the three traits you look for — I think I remember writing it down correctly. Number one was coachability, which is — you and I both know that one — it's one of the traits I look for too. In our game of sales you never, ever stop learning. That's got to be number one for me. I also noticed you said high EQ — and I'd love to come back to that in a second, to talk about what you look for and what you class as high EQ. And then the one that really stood out was the affinity for pipeline generation. And I think that is so true. If you're anything like me — I'd love to hear whether you see this the same way — I've never, ever known an elite salesperson that didn't have an affinity for pipeline generation. They may do it differently, find different means and tactics and strategies. But getting that top of funnel working for them — would you say your experience is similar?. 13:52 Lucy Williams-Jones: 100%. You live and die by pipeline. You need as much good, well-qualified pipeline at the top as possible. Follow the playbook, bring it through, and you'll be successful. I was reading something on LinkedIn yesterday — I can't think who said it, so if anyone listening recognises it, let me know — it was around an SDR who was doing 20% of their potential outreach, but still hitting their numbers because that 20% was quality outreach. And what I was thinking was: imagine if you did 70 or 80%. If you turned it on its head, how much more you could achieve. At the end of the day it's a numbers game, right? If you can put good qualified pipe in, and you do your research, put good discovery meetings in, and pass them through to be great new business meetings — the more you put in, the more you get out. And that's on you. That comes down to work ethic. 15:19 Andy Whyte: You've actually covered all three of my traits: coachability, intelligence and EQ, and an affinity for pipeline generation — with a really heavy pipeline generation mindset, because we know that new logos are the lifeblood of any organisation. Especially an organisation like Datadog — we want to make sure we're landing new customers and growing them, getting value to exactly the right people. 15:36 Lucy Williams-Jones: So yeah, there are lots of ways to test for it. But what I always see in my best people — going back to when I was an individual contributor — I used to love getting an account and getting my markers out, figuring out who's who: who do I need to contact, what's their messaging, which spikes do I need to go after? I absolutely loved that. And I'm trying to instil that now in the team. Slow down to speed up. Do the walk at the front of the funnel. Because if you do the right things early, the rest will follow. Whereas some people rush the front end and then think everything will happen — and it doesn't. Because there are flaws. They haven't lined up the decision criteria before going into the proof of value, and then they're surprised when the customer doesn't sign. They haven't identified what the economic buyer cares about before going into the proof of value. 16:31 Lucy Williams-Jones: So they've done this great proof of value, and then it becomes: "Guys, one more thing — it doesn't do anything I actually need it to do.". 16:31 Andy Whyte: Yeah. You need to make sure you put high quality in, and you're going to get high quality out. And I think that goes back to what you were just saying about the post you read on LinkedIn — the SDR doing 20% quality outreach. I think if we analysed that 20% that progressed, there would be a commonality: it had all of those things you were talking about. The way you described how you used to do pipeline generation is how elite salespeople do it. They're taking the perspective of what's in it for the customer. How can I help the customer? Who will care? Different people will care about different things — which is what you touched on with the economic buyer having a different perspective. We're selling a broad solution that delivers value across many areas, and those different areas of value will score differently for different people inside the same organisation. How do we map that out? How do we catch the right attention? Going back to your point about the person doing 20% — if you zoom in on that 20% and then expand out, focusing on quality over quantity, you start to get this proliferation of success, and that flywheel starts to spin. 17:33 Andy Whyte: And that's no coincidence. The people I've namedroped, the great people you've mentioned — the reason they gravitate together is because they've had success together. It's not some sort of club. It's because they've been successful together and they bring good talent with them. And if you want to be part of that kind of opportunity, you have to focus on the things you were talking about. And it's not something you're born with — but it is a learning process. You've got to be open. One of the things I kept saying at our team meeting last week was: you've got to be open and embrace the sales process, because if you do, it will serve you well. If you close down, cut corners — it will come back to bite you. And it's not about saying "I told you so." It's about: follow the sales process, follow the playbook. 19:41 Lucy Williams-Jones: Whether you're at MongoDB, Datadog, or BMC — the playbook is theoretically the same, with some slight tweaks. They evolve depending on the complexity of the product, or how much demonstration is involved. But believe in the process, and if you believe in the process, good things will come. You know, I'm such a firm believer in that. I've read John's book a number of times, and obviously your book — loved it. And I don't think you're ever too old to learn a new skill or embrace a new way of working. It could change your life. 20:24 Andy Whyte: Yeah. And I want to build on something you said that really struck a chord with me — about being open. I don't know if you found this the same way, but if I think about the most elite salespeople I've ever worked with — and I've had the great privilege of working with some truly elite people — the one thing they all have in common is that they are the most open. They're the first ones to put their hand up and say: "You know what, this deal isn't going the way I'd like" or "I'm losing here." Or if you ask how their year's going: "Not great. I haven't got much on right now." Whereas the opposite of those elite salespeople — they're always talking everything up. And I reflect on this a lot, because I think it comes back to a kind of confidence in your ability. That confidence is, in itself, as a salesperson, a self-fulfilling prophecy. Because if you are that elite salesperson and you walk into an opportunity — via your gut, but also via a qualification framework like MEDDIC — you can see that for whatever reason, whether there's not enough pain, not enough enthusiasm from the customer, you haven't got access to the right stakeholders, the customer doesn't know what their own decision process looks like — you can see those things. 21:00 Andy Whyte: And as that elite salesperson you say: "I'm going to slow these things down to speed them up." And the reaction the customer has to that is: wow, this person isn't prepared to waste their time here. They must be really busy, really valuable. Maybe I should be more interested. Whereas the flip side is salespeople who are almost clutching at straws — and you get into this rut where the customer senses desperation. And we know how that comes across in all walks of life. If someone is trying too hard to get your attention, they come across as desperate. That's a really bad thing. So I love what you said about being open. It's a really nice way of describing it. 22:23 Lucy Williams-Jones: Yeah. And if I think about moving through a sales process — I like to call them gates. When do you close one gate and open the next? We typically spend far too little time in each stage. I say to myself, going back to my earlier days: "Someone's told me they've got a problem, I know we can solve it — let's get to the demo and the new business meeting." But actually, I'm now encouraging my team to spend as much time as possible in discovery mode, to make that new business meeting so impactful. Before you close that gate and move on to the next stage. Because can you really get to the depth of the pain in one 30-minute call? You might get their tech stack, you might understand what they're trying to do — but you need to understand what impact that has on the business. Who cares about it within the business? If a platform went down, what would the implications be across different parts of the organisation? So yeah, I'm really encouraging my team now to stay in discovery stage for as long as they need to. 23:03 Lucy Williams-Jones: You might have multiple calls before you move into that new business meeting — to really be able to showcase the challenges and deliver a demo that's so specific to what they're trying to fix that it becomes a no-brainer. We had an engagement recently, last quarter, where we got a massive pat on the back from the customer — saying that, yes, it was competitive. But from a vendor standpoint, the fact that we took the time to explain the challenges, why we thought we were the right fit, and how we do things differently — that set us apart from every other vendor in that race. 23:45 Andy Whyte: Yeah, I love that. And it's so interesting — because in our sales careers we generally start out selling higher-velocity, shorter-cycle, lower-value deals. And those shorter cycles teach us — perhaps wrongly — that it's good to get to the next stage as quickly as possible. And I think that teaches us the wrong lesson. If you're at stage one and you move to stage two, the deal's more likely to reach stage three, simply because you're at stage two. But what you're effectively saying — and what I completely agree with — is that spending more time in stage one will get you through two, three, four, and five far more quickly. And I really like that way of looking at it. I think it's something we're all guilty of in our industry: measuring success based on progression through stages rather than on how much value we're creating or how much pain we're solving. And you know, I'm sure — what would you rather have? A pipeline full of stage five deals, or the same total value in stage one and two deals — but where those stage one and two deals have twice the amount of pain that you can solve?. 24:54 Lucy Williams-Jones: I think if I phrased it that way, you'd give me a very specific answer. I'm really passionate about this. And I'm really confident that when we engage correctly — following the process, giving a great customer experience — all of the transactions we're working on become solid. I don't like inflated pipeline. It's one of my biggest pet peeves — stuffing pipeline because it looks better on your leading indicators. I want good quality pipeline, because we know it'll come through. It also helps with resourcing. Nothing is worse — I see it and it pains me as a director — when opportunities are in late stages and the evidence just isn't there. I try to make excuses, but I don't anymore. I just say: go back and find out the answers before we even get the technical team involved. I'd rather have a pipeline of strong, qualified opportunities where we're solving customer pain, we've got customer buy-in, and we've identified a potential champion who's going to take us forward. We've got the right decision criteria, and we know we can win. If there's a use case that we're not going to win — I'd rather just call it out. 25:32 Lucy Williams-Jones: And I love your sign there by the way!. 26:12 Andy Whyte: I need to get one for the office. Yeah, I should start selling them. Put them on the MEDDICC shop — forward slash "Nobody regrets qualifying out" neon light. For those listening on the podcast — I'm holding up my MEDDICC T-shirt. 26:12 Lucy Williams-Jones: Yeah, get a Datadog T-shirt and see!. 26:12 Andy Whyte: This is very high quality, by the way — if it's as good as the software, let me tell you this is very good cotton. 26:12 Lucy Williams-Jones: Actually I don't think it is cotton. We apparently have the best quality T-shirts in the industry. 26:12 Andy Whyte: That's a claim. That almost feels like when shows develop a running theme — maybe to appear on this show, you have to give me a T-shirt, and I'll start a league table. What is the technical decision criteria for a Datadog T-shirt?. 26:12 Lucy Williams-Jones: The fabric washes really, really well, and the logo never washes off. The more you wear it and wash it, the better it gets!. 27:59 Andy Whyte: That's just you trying to get me to advertise around the Cambridgeshire village I live in. If you start getting enquiries from retired farmers looking for Datadog kit — that'll be me. 27:59 Lucy Williams-Jones: But hey — wear it ten times and I'll get you a hat as well. 27:59 Andy Whyte: Deal! Now, I can see something in the background. Those paperweights — are those President's Club awards?. 28:41 Lucy Williams-Jones: Yes. So they're from Datadog — we obviously didn't have physical clubs during Covid, so we've got the 2019 and 2020 Lucite awards. Very heavy, great paperweights. And we got a best-of vest as well. Yes — because nobody could travel anywhere. And they've done some other great things since. But I think next year we'll see how close to normal things get and hopefully we can all get together again. 29:05 Andy Whyte: I have a friend whose Presidents Club award was a Nessie — the Scotland trip — but they sent him a backpack because they couldn't run it as a trip. He was supposed to be going to the Bahamas for a week. So knowing that he's not the only one who got "paper-weighted" or given a backpack — yeah, it's all good. Patagonia is great quality. I don't know, I think I'm sitting on a backpack from the best President's Club I ever went on — around 2001. I think I'll speak for everyone listening when I say: as much as I love Patagonia backpacks, I prefer the vacation. But well done nonetheless. So — you had Covid, right? And not lightly, as I understand?. 30:30 Lucy Williams-Jones: Very poorly. And I think, you know, maybe I had an epiphany. It was kind of what made me shift from thinking about staying as an individual contributor to going into leadership. So I got sick in January — when the real wave of it hit — and I think everyone was getting it then. I'd been sitting up in the Cotswolds, not knowing anyone, definitely not going out. It was either the builder or the neighbour who gave it to me — one of those two. My husband didn't get it, but I was really poorly. From around January 7th until early February — really, really sick. And then there was about a week where I genuinely thought this might be serious. The NHS and the district nurse were checking in on me, and my oxygen went down to 82 — which makes it very hard to breathe. For about four days I was lying there thinking: if anything did happen to me, I'd only ever really be known for being a great salesperson. And hang on a minute — 20-year consecutive Presidents Club back to back, that's pretty impressive — but I'm more than that as a person. 31:39 Lucy Williams-Jones: I've learned so much from so many amazing people over 22 years. The likes of Adam Quartermaine — who's now at Sprinklr — Don Darcy at MongoDB, Cédric who's still at BMC, Jason, Andrew, Patrick — I've learned so much. And I just thought: I want to pass that on. That's what made me change. So as soon as I got better, I rang my boss Tony and said: "You've been asking me if I want to go into management — I've always said no because I manage my own diary and know what I'm doing. But I want to give it a shot." And you know, I'm very lucky to have such a great management team and great peers around me. Because going from individual contributor to director is a whole new world. What I cared about for me, I now care about for six times that. I'm lucky to have peers like Dan — we work really, really closely together and we're absolutely aligned on the playbook and MEDDIC. But yeah — I wanted to take that knowledge and try to help other people live their best life. 32:39 Lucy Williams-Jones: And if you follow the playbook, it could change your life — financially, professionally, and personally, right? There is nothing I love more than getting a transaction over the line. Not just for the financial reward, but for the customer — and for the champions I've met over the years, some of whom I'm now genuinely good friends with. I'm in London, we go out for drinks — people I worked with ten or fifteen years ago. And the beauty there is not just the personal connection. Somewhere right now, one of your champions might be on a podcast relating to their industry, talking about their successes — and they'll probably reflect on some of the solutions you worked on together that made them successful. And that comes back to the vested interest aspect of the champion. They're the best salespeople out there, whether they realise it or not. With those champions you stay close with — because you found a personal connection with them, you were able to tap into the things that drive and motivate that person. And that's what makes us good champion builders — we can align ourselves to their direction, their goals. Because every champion is different. 33:16 Lucy Williams-Jones: I always use the example of a guy I really like at Selfridges — which most people know from the TV show with Jeremy Piven. He's been there 20-odd years. 34:38 Lucy Williams-Jones: If you took the same champion-building approach you'd use with someone who's super career-hungry, wanting the next big promotion — and applied that to someone who's been at Selfridges for 20 years and is never leaving — that's not going to work. It's about tapping into their thing. 34:38 Andy Whyte: So I love that. One of the things I'm really interested to hear about is your learnings from making the jump from individual contributor to leader. And from a different angle — things you might do differently, with hindsight. 35:41 Lucy Williams-Jones: Oh, the question could be one of those where you need to cut things down because I could talk for hours. So — as an example, everyone who joins Datadog goes through an onboarding process. It's great. Enterprise onboarding is really well received. The first week when I joined was in person in Boston — and although that's currently on pause because of Covid — what I wanted to do was put myself in the shoes of someone starting at Datadog from day one. What would I need in my toolkit to be successful more quickly? What would help me ramp faster? Because a typical enterprise salesperson ramps in roughly six to nine months. So I had this goal of getting my reps ramped in four to five months — reducing that ramp by maybe 50% — because then they'd be ready to go all guns blazing in January. So in every interaction I have, I try to put my individual contributor hat on and give guidance from that standpoint. Start with the why. I read an article recently — it said: don't write in Slack "I need this" or "I want this." Instead explain why you're asking for it, because it's going to help the person do X, Y, Z. 36:29 Lucy Williams-Jones: Laying that out is really important. Setting the stage, setting the scene, adding context, building on the playbook. One of the first things I do after the first week is walk the team through the playbook — talking through each of the different stages, how it aligns to MEDDIC at each stage, and when you should exit and say: "You know what? This isn't for us. Let's move on." I work with someone called Nick Hewitt, and he is the best person I've ever seen at running an initial discovery call — qualifying in or out. And he does it in such a way that you're like: fair play. He's not wasting the customer's time, and he's not wasting his own time. It's not a fair exchange of value otherwise. 37:29 Andy Whyte: What does he actually do to make it so effective?. 37:29 Lucy Williams-Jones: He checks in with everyone on the call — but then he goes straight to the chase. These are the three challenges that organisations like yours typically face and that we could potentially help with — whether you're using our tools today, open-source alternatives, or native cloud tooling. These are the downstream consequences of those approaches. Are you experiencing any of them? And if they say: actually, no — great. See you later. Typically, Datadog is a fit for three key use cases: building out a cloud observability practice, adopting a DevOps mentality, or migrating to cloud infrastructure. Those are the three key areas we try to attach to. And there's nothing wrong with going on a discovery call, asking those questions, and hearing: "You know what? We're fully on-premises. We've got no cloud migration or DevOps model in place." And then saying: "You know what? Let's draw a line under it. Maybe in another six months we'll work together." Nick is amazing at that. 38:14 Lucy Williams-Jones: And I think we're often too scared of saying no as salespeople. We want to hold on to anything — "Someone's talking to me! Someone said yes!" But then we waste time — both ours and the customer's — promising we can do something when we can't. 38:36 Lucy Williams-Jones: So yeah: qualify out early, be strong, believe in what you're doing at discovery stage. If you need to spend longer there, do it. And then follow the playbook. Because if you follow the playbook, you'll be super successful. 38:36 Andy Whyte: Yeah. And a big part of that — I think — is not just what Nick says, but the persona he brings to the table. The customer sees that this is a person who's genuinely trying to understand whether there's real value — not just whether there's a deal in it for him. And the big difference is: this isn't just "is there a deal here?" It's: "Is there enough opportunity for this to be worth a 90-day evaluation process?" In an organisation like Datadog — that's roughly what a full evaluation takes. Why would you enter into that if you didn't think there was going to be a real opportunity at the end? And it does come from the customer side too — you don't want to lead people down the garden path. Knowing when you're not the right fit is really important. And actually, doing that very early on — if you've got a champion or you're building that relationship — because when someone is that honest with you early on, it sets the tone for the entire engagement. 39:17 Lucy Williams-Jones: Yeah. Succinct. And I've learned a lot from Nick myself. I'd known him previously — we'd been at Datadog together for a while, and our paths had actually crossed at BMC too, just in different teams. It's a different style — maybe I'm too nice sometimes, not quite as direct. 39:53 Andy Whyte: Yeah. And that's something I always emphasise with MEDDIC — it's your own style, your own personality that overlays on top of the framework. No methodology should try and change who you are, because people do buy from people. It's very seldom someone buys from someone they don't like or trust. So when you say you're too nice — maybe there are deals Nick will save time on that you might not. But there'll also be deals you win that Nick might not — because someone will find his directness a bit too much, whereas your warmth and openness resonate with them. It always balances out. And I think that's one of the reasons I love MEDDIC so much — it sits underneath your personality, underneath your style, as that extra layer of intelligence you can refer to. You can look at the evidence and say: I think this person is a champion, but let me check the evidence. I think this is the decision criteria, but let me validate it. And then you can pivot if the MEDDIC evidence contradicts your gut. 40:35 Andy Whyte: That's one of the things I'm always keen to point out — because sometimes with methodologies like Challenger, for example, which is very good — Challenger says there are four types of salesperson and you should aspire to be the Challenger type. But if you're one of the other three, it's asking you to change. And that can be one step too many on top of all the other things salespeople are already trying to do. Whereas the beauty of MEDDIC is it's not asking you to change. It's just giving you a framework to point you in the right direction. 42:17 Lucy Williams-Jones: Yeah. And coming back to hiring — I encourage all of my team to bring their own ideas to work. We don't want robots. We want everyone to bring their own way of doing things — because I know for a reason they've been successful. They know what they're doing. So don't think you have to change yourself and become robotic. Be yourself, because people buy from people. We don't want a machine producing identical enterprise reps. 42:17 Andy Whyte: Yeah, agreed. So — I got complaints from people on earlier episodes because I always ask what the most important part of MEDDIC is. And in the last couple of episodes I stopped asking, and people complained. They want to hear what you think. So, by Alexa — what is the most important part of MEDDIC?. 45:02 Lucy Williams-Jones: Yeah, it's like picking a favourite child — I don't have children but yeah, I've got to answer. So my favourite, the one I believe you can never close a deal without, is the Champion. I think all the letters and all the components of MEDDIC are important and interdependent. But if you don't have a champion, you're not going to get a deal done — because there's no one selling for you when you're not in the room. There's no one to take you to the sponsor, to tell you about the decision criteria, to navigate the process. So I would say Champion, probably followed by Pain, underpinned by Metrics — because Metrics will always come back together with Pain in the end. You know, it's hard to pick just one. But Champion — because back in the day, building champions over lunches and dinners — that was how it was done. They say champions are built on the golf course. My golf handicap is terrible. My golf game is not my golf course. But now I think champions are super important. And as I said, I've got friends now that I worked with ten years ago who I still speak to. 45:57 Lucy Williams-Jones: There's someone I met at BMC when I was working on JP Morgan — he's been in Dubai for a while now — but he always comes back to me because he knows the value we delivered last time. He always comes back. And it's amazing, really. 46:14 Andy Whyte: And I think what you're describing is someone who recognises you as a person who can deliver value — not just from your solution, but from yourself. And I think that's a really important part of modern sales. The most elite salespeople are seen by their customers as consultants, not salespeople. They're seen as people who come in with a consultative, value-driven approach. That person sees you as someone they can trust and learn from whenever they engage with you. And then I love what you said about all the things you need a champion to do. Because when the going gets tough — and it inevitably will at some point in any deal — price objections, stakeholder objections, a competitor taking the lead — if you try to overcome those through the standard routes without a champion, it's incredibly hard. So I do tend to agree. I'll say I'm always slightly conflicted about the idea that you can't find a real champion without having a real pain for them to solve. It's chicken-and-egg for me. 47:39 Lucy Williams-Jones: I think that's not quite right though. You might have a really strong champion who moves between organisations. They may not have the pain right now — let's say they haven't migrated to cloud yet — but they know when they do, they're going to have these problems, and they still reach out to you now, because of the value you delivered previously. So I do think in the initial stages of building a champion, pain is super important — because you want to make sure there's something professionally in it for them. There's always something in it for a champion, right? Whether it's a promotion, getting their head above the parapet, or eliminating those 3am calls because something's gone wrong. Without solving a real pain, you wouldn't have that. But a true champion will continue to advocate for you even after that initial engagement — and you'll probably sell to them multiple times across your career. I don't necessarily think pain is always a prerequisite if you've already built that relationship and they're a true champion. For me, if you could look at MEDDIC from the outside, the Champion would always be in the centre — because you're never going to reach the economic buyer unless you've got one. 49:01 Lucy Williams-Jones: And you can try going above people's heads without a champion — I did it once, and it was horrendous and caused a lot of problems. One of my core beliefs is: use your champions to navigate the organisation, because that's what they're there for. And if they're not taking you there, ask yourself why — because that's a signal that something might be wrong. And this all comes back to the work you do right at the beginning: mapping out the organisation, getting a feel for who cares about what, who's impacted by what, who's motivated by what. 49:41 Andy Whyte: That is elite-level selling. And that's why you've had the success you have. I love that — you can tell by the way you're thinking about these deals. How can I attach value to this scenario? How can I ensure the value resonates with the person I'm working with? That's what drives it all forward — or sometimes tells you there's not enough value there, and we know what that means. Call it out. 49:41 Lucy Williams-Jones: The biggest thing for me as well: if I've got a champion, my competitor's probably got a champion too. So I take great pleasure in identifying the competitor's champion and converting them. That's my favourite move. Getting my existing champion and the newly converted champion in the same room — happy families. But you better believe that if you're working with someone, one of your competitors will also have a champion there. So it's like: who has more influence? The power base model — who's going to step out of their comfort zone to fight for their vendor in the wider organisation? In an ideal world, everyone would be your champion. But that's never going to be the case. So it's about how you neutralise the competition and how you leverage your champion to be more powerful than theirs. 50:25 Andy Whyte: And that's where the beauty of the other parts of MEDDIC you talked about come into play — the vested interest, breaking down the decision criteria so that what you do differently or better than the competition is squarely on the table. 51:15 Lucy Williams-Jones: So yeah. I've actually made, as part of working through your book, a really useful deal sheet that I use to track champion progress. There's one specific element — the Champion Funding piece — probably from BMC days — that I really got into: identify, build, test, and use a champion. The identification piece is going to be really key. Stay in that stage for as long as you need to — make sure they are the right person, because someone can look like a champion on the surface and not be one. The identification and the building are probably the two most important stages. If you do those well, the rest is easier. Put everything into the front end — loads of time, loads of considered care — and the rest will follow. Make sure you identify them right, build them correctly, and give them value. It's all about fair exchange of value. Using your champion should come after that. I've got someone I work with at Vodafone — I remember we were online, last day of the financial year, it was 10:59pm because the deal was based out of Amsterdam and it was 11:59pm there. I mean, it's like trying to get the PDF across — thank God we don't have fax machines anymore. 53:13 Andy Whyte: Yeah — I started out wrestling a fax machine in the office on the last day of the month. Now it's DocuSign. 53:13 Lucy Williams-Jones: But yeah — a champion will go above and beyond at 10:59pm on the last day of the year to get you that transaction over the line. And that's what they stand for. And the beautiful thing was: it wasn't just me who was committed — it was him too, because of the value he was going to get from it. We both fought for it together. It came in with about 30 seconds to spare, I think — there's a time stamp to prove it. 53:54 Andy Whyte: I love it. Those are the stories that you share with your teams — getting them psyched up for quarter end or at the start of a quarter — saying: there will be moments in this quarter that we'll be talking about for the rest of our careers, hopefully around a bar some day. And that's a perfect example of exactly that. One thing you said just at the end really stood out — you were talking about the different stages of working a champion: identify, build, test, and use. I think using your champion is something we as an industry sometimes overlook. We focus on building and testing, but actually deploying them — putting them into play. I've had sessions with sales teams where I've had to say: as much as we often end up friends with our customers, that's not the primary objective. 54:31 Lucy Williams-Jones: And in your example — yes, some of those champions have become real friends, and yes there were moments where I thought I might lose both the friendship and the deal because I had to be very direct with some of them. But some of them went on to buy from me again further down the line. So using them isn't about exploiting the relationship — it's about coaching them and putting them into play. Sharing decks, sharing ideas, preparing them for the economic buyer meeting. Because they're going to walk in and it's going to be incredible. You're going to give them the accolade of: "We're here because of this person. Now here's what we want to understand from you." So yeah — champions, hands down, the most important for me. 55:11 Andy Whyte: And I'm going to ask you to say it now: you won't close a deal without a champion. 55:11 Lucy Williams-Jones: No — you won't. And I've tried to convince myself otherwise, tried to navigate around it — but no. Never. 55:11 Andy Whyte: Just before we wrap up because we're running out of time — for those listening who haven't had the opportunity to work at a company that does proof of values the way Datadog does them with POVs: could you give us a two-minute overview of what that process is, and how it works?. 56:28 Lucy Williams-Jones: Well, as a private company — we want to make sure we follow it. So: we've done a great discovery, we've spent the right amount of time there, we've moved into an amazing new business meeting where we've articulated the challenges, how Datadog is going to fit, how we're going to help. We then get agreement to move to a proof of value. First — we make sure we've met with the economic buyer. These criteria are documented. And then we go through a very structured process ensuring that all of the criteria we need to hit within that POV are documented and tracked as part of the decision criteria. We use our unique differentiation to make sure we're pushing the needle towards that decision criteria, to make sure we win. And then we go hands-on. We work really closely with the technical team — we've got some really talented people here — and they're very stringent about owning the champion-side throughout. So as the champion goes through the POV, seeing what we can do over three to four weeks, at the end of it we do a readout. 57:41 Lucy Williams-Jones: There are a number of touchpoints throughout, all geared around collecting metrics, ensuring the decision criteria is validated, reviewing where competition stands and where we can do it better, making sure we're aligned to the pain, and making sure the champion gets a win at the end of it. We then do a pre-readout and typically enter into commercials. Now a POV like I've done before with other large organisations that has lasted three to six months — at the end of the day, I don't think you need that long. However complicated your software is: a proof of value is about proving the value they're going to get for the pain they've got. It's not about bits and bytes or feature lists. It's about what can we give to you as an organisation that's going to solve that high-level pain — and here are the metrics to back it up. 58:25 Andy Whyte: I love it. Thank you for that. I love the way you describe it — you can tell how orientated it is around value. And I think a lot of people listening are used to the phrase "proof of concept." And I've always had that challenge: we've got hundreds of customers, why do we need to prove the concept? The concept works. But "let's prove that this concept has value for you specifically" — that's a completely different conversation. And it's clear from everything you've said — the decision criteria, the metrics, the value framework running all the way through. That's why this is such a big part of your playbook. I think a lot of people listening will take a lot from that and reflect on how they do similar things and how they can embrace MEDDIC as a tool to increase their success rates — but also the efficiency with which they run those evaluation cycles. 59:20 Lucy Williams-Jones: Yeah. It's about accelerating, de-risking, and making sure there's value at the end of it. Anything you use to accelerate a sales cycle — using Metrics, for example — supports that, because it allows you to be really clear and concise on the gaps. I actually hate a MEDDIC sheet that's all green — because if it's all green, it should already be closed. I want to see gaps. Every week with the team we look at different deals and go through where the gaps are, then build a plan for how we go and address them. Whether it's: we don't have enough metrics — who do we need to go to to get them? Metrics need to be really, really strong. So yeah — we live and breathe by the MEDDIC sheets and the metric process to make sure we're giving a great customer experience, a fair exchange of value, and that we're de-risking and accelerating. Because that's what every software or hardware company needs to do.